Thursday , May 26 2022

My Sissy Roommate

“Relax, Andrew. It’s just a party. Yeah, sure there will be girls there, but it’s not like they’re serial killers or something,” I tell my best friend as we make our way to the party.

I swear he’s always like this. So worried about everything. I don’t know how the kid has survived this long. Probably because I’m always here to calm him down.

It’s kind of funny, not many people can see Andrew and me as being friends. Him being a meek, petite, nerd who’s often confused as a girl and me a muscle-bound, jock who gets all the girls. We’re complete opposites from each other.

And yet, Andrew and I have always been best friends. We grew up next door to each other, I’m always the one getting him into trouble, and he’s the one who tries to think a way out of it. Of course, he used to get picked on a lot in high school, but not when I’m around.

He and I are like peanut butter and jelly. Oil and vinegar. Wine and cheese. Milk and cookies. What I’m saying is, we just work well together.

I couldn’t imagine going to college without him.

We arrive at a party at a classmate’s sorority, she begged me to come after class. The place is packed with girls everywhere. Definitely a lot more girls than guys.

Sarah’s eyes light up as she sees me. Her blonde hair neatly coming down to her shoulders. “You came!”

“I told you I would,” I laugh. “This is my roommate and best friend, Andrew. Andrew, this is Sarah, the girl in my math class.”

“It’s nice to meet you,” she says. “Do you guys want something to drink?”

“Yeah, sure,” I shrug.

We follow her through the house, into the kitchen, where a giant jug cooler is. She grabs two cups and hand them to us. “Normally we charge $5 per cup for guests, but you two can drink on me.”

“Aww, thanks. Such nice hospitality.” I give her my heart-stopping smile which turns her cheeks pink. I can admit she has really beautiful eyes. So green and verdant.

We fill our cups with jungle juice and follow Sarah out to the back porch.

“So, how long have you two been friends?” she asks.

“Since kindergarten,” I laugh.

“Wow, that’s so cool,” she says.

“Yeah, we grew up next door to each other,” he adds.

“It’s so rare to have remain best friends in college, more power to you,” she says.

“What about you? You still with your best friend?” I ask.

“Well, not really. We sort of broke up in high school,” she says.

“Ouch, what happened?” I ask.

“She fucked my now ex-boyfriend behind my back,” she says.

“Ouch, what a bitch,” I say.

“Truly backstabbing,” she says.

“Definitely not a true friend,” I add.

“Yeah, not like the two of you, I’m so jealous,” she says. “But, I do have some pretty cool friends in the sorority.”

“Nice, we’ve made some friends as well. So what made you join a sorority?” I ask.

“My roommate convinced me, speaking of her, here she is!” A girl with dark brown hair and matching eyes walks up. “Becca, this is the boy from my math class I was talking about! Arthur, meet my roommate, Becca.”

I hold out my hand and she shakes it as she stares into my eyes. “It’s nice to meet you, Becca.”

“You too! Sarah has been talking nonstop about you,” she says.

“Has she?” I ask, raising an eyebrow. “And what mean things has she said about me?”

“Oh trust me, it’s all good. And you definitely add up to her stories,” she says. “With all the good things she’s said about you, I was beginning to think you weren’t real.”

“Well, I hope not to disappoint,” I say, giving her my lady killer smile. “By the way, you should meet my roommate.”

“You mean there are two of you?” she asks.

“No, Andrew is far smarter than I am,” I laugh as I put my arm around him. He tenses up as her eyes fall upon him. Her expression changes from giddy anticipation to a look a girl would give to a puppy. Not exactly what I was hoping for.

“Aww, he’s adorable,” she says. “You know, you’d be so perfect for my social experiment.”

“Oh, Bec, don’t!” Sarah says.

“Aww, come on Sarah. You know he’d look so good.”

I raise an eyebrow as Becca grabs Andrew’s hand and pulls him behind her. “Come, you need to meet my partner, Kenzie.”

Sarah grabs my hand. “We should probably follow them.”

“What’s her social experiment?” I ask.

“Ehh, you’ll see,” she says.

I follow her into the house and I see Becca talking to another girl with red hair. They both look at Andrew with excitement before dragging him upstairs. Sarah and I follow after them.

We go into one of their rooms where Becca and the red-headed girl who must be Kenzie are holding girl clothing against Andrew’s frame. The look on his face says it all. Shock, embarrassment, humiliation and if I wasn’t mistaken, a little bit of excitement.

“Come on, you should definitely try these on for us,” Becca says.

“I was afraid this would happen,” Sarah says as she drags me into the room and shuts the door. “Come on guys, don’t do this.”

“Aww, come on Sarah. Don’t be a buzz kill. You know he’d look cute all femmed out.”

“Wait, you want to dress him up as a girl?” I ask.

Andrew looks equally mortified and giddy.

“Don’t you think he’ll look so cute with this skirt on?” Kenzie asks holding up the skirt against his waist. Her eyes go wide as she brushes against his crotch. “Oh my god, do you have a boner?”

“No!” he stammers.

“Yes you do!” she says. “You’re enjoying this as much as we are!”

“I… I…” Andrew studders.

“Don’t be ashamed,” Becca says. “I think it’s so hot. You have to do it now. Just try on a few outfits. Please.”

Andrew’s eyes meet mine. He looks frozen. I’m not sure if he wants me to get him out of this situation or give him permission.

“Come on girls, just leave him alone. Look, Andrew. You don’t have to do this,” Sarah says.

“Oh come on, Sarah. Don’t act like you’re not into this. You were so into it when we were discussing it earlier,” Becca says.

“Yeah, it’s fun to talk about it, but to actually force someone to do it is another thing entirely,” she says.

“We’re not forcing him, we’re just persuading him,” Kenzie says.

“What do you think? You’re his best friend?” Becca says.

“It’s not up to me, it’s up to him,” I say.

Kenzie leans in a whispers something in his ears and his eyes light up.

“So, will you do it?” she asks.

“Okay, okay, okay!” he says.

“Wow, what did you say to him?” I ask.

She smiles. “Just offered him a blow job.”

“Kenzie!” Sarah stammers.

“Relax, it’s just a blow job,” she says.

“Not really,” I laugh. Andrew glares at me.

“What do you mean?” she asks.

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